 
data_exp_13 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H21 N O5' 
_chemical_formula_weight          295.33 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    5.94010(10) 
_cell_length_b                    10.65600(10) 
_cell_length_c                    23.6934(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1499.74(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     25507 
_cell_measurement_theta_min       4.53
_cell_measurement_theta_max       74.658 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.48 
_exptl_crystal_size_mid           0.42 
_exptl_crystal_size_min           0.26 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.308 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     0.815 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6958 
_exptl_absorpt_correction_T_max   0.8161 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             33653 
_diffrn_reflns_av_R_equivalents   0.0632 
_diffrn_reflns_av_sigmaI/netI     0.0216 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -29 
_diffrn_reflns_limit_l_max        29 
_diffrn_reflns_theta_min          3.73 
_diffrn_reflns_theta_max          74.72 
_reflns_number_total              3062 
_reflns_number_gt                 3039 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0516P)²+0.3580P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.07(14)
_chemical_absolute_configuration  'ad' 
_refine_ls_number_reflns          3062 
_refine_ls_number_parameters      190 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0321 
_refine_ls_R_factor_gt            0.0318 
_refine_ls_wR_factor_ref          0.0860 
_refine_ls_wR_factor_gt           0.0858 
_refine_ls_goodness_of_fit_ref    1.089 
_refine_ls_restrained_S_all       1.089 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.16416(15) 0.31226(9) 0.65452(4) 0.0163(2) Uani 1 1 d . . . 
H1A H 0.2175 0.3849 0.6511 0.024 Uiso 1 1 calc R . . 
O5 O 0.77691(16) 0.56057(8) 0.62624(4) 0.0155(2) Uani 1 1 d . . . 
O4 O 0.40815(16) 0.51878(9) 0.64492(4) 0.0188(2) Uani 1 1 d . . . 
O2 O 0.39301(16) 0.04268(9) 0.71947(4) 0.0204(2) Uani 1 1 d . . . 
O3 O 0.04171(16) 0.11026(9) 0.70337(4) 0.0180(2) Uani 1 1 d . . . 
N1 N 0.67960(19) 0.36993(10) 0.65443(5) 0.0136(2) Uani 1 1 d . . . 
H1B H 0.8101 0.3445 0.6411 0.016 Uiso 1 1 calc R . . 
C11 C 0.6061(2) 0.48643(12) 0.64211(5) 0.0145(3) Uani 1 1 d . . . 
C6 C 0.4033(2) 0.16653(11) 0.60249(5) 0.0140(3) Uani 1 1 d . . . 
C9 C 0.2645(2) 0.11605(12) 0.69787(5) 0.0138(3) Uani 1 1 d . . . 
C7 C 0.5465(2) 0.28540(12) 0.68943(5) 0.0133(3) Uani 1 1 d . . . 
H7A H 0.4914 0.3327 0.7226 0.016 Uiso 1 1 calc R . . 
H7B H 0.6461 0.2178 0.7035 0.016 Uiso 1 1 calc R . . 
C4 C 0.6622(3) 0.05803(13) 0.54061(6) 0.0198(3) Uani 1 1 d . . . 
H4A H 0.8045 0.0196 0.5345 0.024 Uiso 1 1 calc R . . 
C12 C 0.7346(2) 0.69322(12) 0.61036(5) 0.0163(3) Uani 1 1 d . . . 
C5 C 0.6111(2) 0.10903(12) 0.59320(6) 0.0163(3) Uani 1 1 d . . . 
H5A H 0.7182 0.1046 0.6229 0.020 Uiso 1 1 calc R . . 
C1 C 0.2468(2) 0.16999(13) 0.55884(6) 0.0197(3) Uani 1 1 d . . . 
H1C H 0.1037 0.2075 0.5649 0.024 Uiso 1 1 calc R . . 
C8 C 0.3426(2) 0.22462(12) 0.65964(5) 0.0139(3) Uani 1 1 d . . . 
C13 C 0.5938(3) 0.69841(14) 0.55701(6) 0.0215(3) Uani 1 1 d . . . 
H13A H 0.6702 0.6520 0.5269 0.032 Uiso 1 1 calc R . . 
H13B H 0.5740 0.7860 0.5455 0.032 Uiso 1 1 calc R . . 
H13C H 0.4462 0.6606 0.5642 0.032 Uiso 1 1 calc R . . 
C3 C 0.5055(3) 0.06314(14) 0.49704(6) 0.0230(3) Uani 1 1 d . . . 
H3A H 0.5405 0.0287 0.4611 0.028 Uiso 1 1 calc R . . 
C2 C 0.2986(3) 0.11875(14) 0.50639(6) 0.0239(3) Uani 1 1 d . . . 
H2A H 0.1910 0.1220 0.4768 0.029 Uiso 1 1 calc R . . 
C10 C -0.0395(2) 0.00980(14) 0.73936(6) 0.0217(3) Uani 1 1 d . . . 
H10A H -0.2042 0.0129 0.7413 0.033 Uiso 1 1 calc R . . 
H10B H 0.0232 0.0198 0.7774 0.033 Uiso 1 1 calc R . . 
H10C H 0.0078 -0.0712 0.7238 0.033 Uiso 1 1 calc R . . 
C14 C 0.6287(3) 0.76351(13) 0.65950(6) 0.0215(3) Uani 1 1 d . . . 
H14A H 0.7269 0.7573 0.6926 0.032 Uiso 1 1 calc R . . 
H14B H 0.4817 0.7266 0.6683 0.032 Uiso 1 1 calc R . . 
H14C H 0.6091 0.8520 0.6493 0.032 Uiso 1 1 calc R . . 
C15 C 0.9720(2) 0.74136(14) 0.59950(6) 0.0216(3) Uani 1 1 d . . . 
H15A H 1.0381 0.6955 0.5677 0.032 Uiso 1 1 calc R . . 
H15B H 1.0643 0.7285 0.6333 0.032 Uiso 1 1 calc R . . 
H15C H 0.9662 0.8311 0.5905 0.032 Uiso 1 1 calc R . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C8 1.4177(15) . ? 
O1 H1A 0.8400 . ? 
O5 C11 1.3396(16) . ? 
O5 C12 1.4841(15) . ? 
O4 C11 1.2274(16) . ? 
O2 C9 1.2067(16) . ? 
O3 C9 1.3310(16) . ? 
O3 C10 1.4512(16) . ? 
N1 C11 1.3479(17) . ? 
N1 C7 1.4574(16) . ? 
N1 H1B 0.8800 . ? 
C6 C1 1.3913(18) . ? 
C6 C5 1.3953(19) . ? 
C6 C8 1.5321(17) . ? 
C9 C8 1.5408(17) . ? 
C7 C8 1.5445(17) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C4 C3 1.391(2) . ? 
C4 C5 1.3928(18) . ? 
C4 H4A 0.9500 . ? 
C12 C13 1.5169(18) . ? 
C12 C14 1.5208(18) . ? 
C12 C15 1.5221(19) . ? 
C5 H5A 0.9500 . ? 
C1 C2 1.392(2) . ? 
C1 H1C 0.9500 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C3 C2 1.382(2) . ? 
C3 H3A 0.9500 . ? 
C2 H2A 0.9500 . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C8 O1 H1A 109.5 . . ? 
C11 O5 C12 120.31(10) . . ? 
C9 O3 C10 114.96(11) . . ? 
C11 N1 C7 121.12(11) . . ? 
C11 N1 H1B 119.4 . . ? 
C7 N1 H1B 119.4 . . ? 
O4 C11 O5 125.11(12) . . ? 
O4 C11 N1 123.86(12) . . ? 
O5 C11 N1 111.03(11) . . ? 
C1 C6 C5 119.05(12) . . ? 
C1 C6 C8 119.26(12) . . ? 
C5 C6 C8 121.68(11) . . ? 
O2 C9 O3 123.89(12) . . ? 
O2 C9 C8 123.04(12) . . ? 
O3 C9 C8 113.05(11) . . ? 
N1 C7 C8 115.13(10) . . ? 
N1 C7 H7A 108.5 . . ? 
C8 C7 H7A 108.5 . . ? 
N1 C7 H7B 108.5 . . ? 
C8 C7 H7B 108.5 . . ? 
H7A C7 H7B 107.5 . . ? 
C3 C4 C5 120.17(13) . . ? 
C3 C4 H4A 119.9 . . ? 
C5 C4 H4A 119.9 . . ? 
O5 C12 C13 109.83(10) . . ? 
O5 C12 C14 110.18(10) . . ? 
C13 C12 C14 113.07(11) . . ? 
O5 C12 C15 101.96(10) . . ? 
C13 C12 C15 110.95(11) . . ? 
C14 C12 C15 110.30(11) . . ? 
C4 C5 C6 120.35(13) . . ? 
C4 C5 H5A 119.8 . . ? 
C6 C5 H5A 119.8 . . ? 
C6 C1 C2 120.35(14) . . ? 
C6 C1 H1C 119.8 . . ? 
C2 C1 H1C 119.8 . . ? 
O1 C8 C6 111.51(10) . . ? 
O1 C8 C9 108.65(10) . . ? 
C6 C8 C9 106.69(10) . . ? 
O1 C8 C7 110.44(10) . . ? 
C6 C8 C7 112.86(10) . . ? 
C9 C8 C7 106.40(10) . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C2 C3 C4 119.53(13) . . ? 
C2 C3 H3A 120.2 . . ? 
C4 C3 H3A 120.2 . . ? 
C3 C2 C1 120.53(13) . . ? 
C3 C2 H2A 119.7 . . ? 
C1 C2 H2A 119.7 . . ? 
O3 C10 H10A 109.5 . . ? 
O3 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
O3 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C14 H14A 109.5 . . ? 
C12 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C12 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C12 C15 H15A 109.5 . . ? 
C12 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C12 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              74.72 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.193 
_refine_diff_density_min   -0.310 
_refine_diff_density_rms    0.067 
